3780-33-4Relevant articles and documents
Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
Iguchi, Daniela,Erra-Balsells, Rosa,Bonesi, Sergio M.
, p. 1903 - 1910 (2016/04/05)
Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two consecutive reaction pathways are proposed. The former involves the photo-Fries rearrangement of the esters in all the solvents studied and, depending on the proticity of the solvent, the latter involves an ESIPT process followed by thermal 6π-electrocyclic reaction and/or thermal (intramolecular oxa-Michael addition) cyclization of the ortho regioisomers photoformed. This second pathway is responsible of the formation of the 2,2-dimethylchroman-4-one derivatives.
Modification of hydroxybenzopyranoids: Facile deoxygenation of 2,2-dimethyl-7-hydroxy-4-chromanones and a new approach to their novel mercapto analogs
Sebok,Timar,Eszenyi,Patonay
, p. 6318 - 6321 (2007/10/02)
A facile deoxygenation of a systematic series of substituted 2,2-dimethyl-7-hydroxy-4-chromanones via their sulfonate, isourea, and thiocarbamate derivatives is reported. The synthesis of novel 2,2-dimethyl-7-mercapto-4-chromanones has been accomplished b
On the synthesis of substituted 2,2-dimethyl1-4-chromanones and related compounds
Seboek, Peter,Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 2791 - 2794 (2007/10/02)
A systematic study of the reaction of a series of monosubstituted phenols 3 and 3-methylbut-2-enoic acid 4 in phosphorus oxychloride/zinc chloride revealed that the formation of 4-chromanones was strongly infuenced by the substituents and their position on the aromatic ring of the starting phenols.